Michael Bloomberg, Ray Kelly talked 11th-hour New York City mayoral run

Kelly left the meeting with Bloomberg serious about being a candidate. | AP Photo

Still, Kelly continued to consider a run amid repeated pleas from people who saw him as the best option in the post-Bloomberg era. For many of the city elites, Kelly was the obvious alternative to the candidates running, including Morgenthau, with the logic being that Kelly might change his mind if enough people appealed to him. “[Kelly] has to hear from people, there has to be a groundswell,” said one leader who heard from the effort, recalling the argument.

Kelly is one of the few administration officials who meets with Bloomberg one-on-one, and so exactly what was said in the meeting they held about the mayoral run remains between them.

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But according to people familiar with the conversation, the often non-confrontational mayor didn’t stop Kelly from running, but did not commit support. At the time, a close Bloomberg ally, City Council Speaker Christine Quinn, was running in the Democratic primary, and Anthony Weiner hadn’t yet imploded.

Bloomberg pointed Kelly toward his top political aide, Howard Wolfson and his 2009 campaign manager Bradley Tusk, who both met with the police commissioner.

Not long after, Kelly made a decision: his mayoral campaign was finally, officially dead.

“It was on,” said one of the people involved, “and then it was off.”

There was talk of looking into whether Republican candidate John Catsimatidis — who’d earlier in the cycle said he’d step aside if Kelly ran — would consider a time-sensitive legal maneuver to turn over the third-party “Jobs Jobs Jobs” ballot line he’d sought, or even the GOP line, but a senior adviser to Catsimatidis’s campaign said the ask was never actually made.

The weeks leading up to his meeting with Bloomberg were a blur of rushed planning. Involved in all of it, though, was Kelly’s son Greg, a morning anchor for New York’s Fox affiliate, the commissioner’s strongest advocate, according to several sources.

Greg Kelly asked Trippi and Caddell, both Fox News contributors, to talk to his father. Greg Kelly received a campaign strategy memo from Rollins — who was not told about the Caddell or Trippi meetings — and who had already begun reaching out to Republican operatives that included pollster Ed Goeas and media consultant Larry McCarthy. After the Bloomberg meeting to say he was running. Greg Kelly reached out to people whom he’d brought into the conversation—“we’re going,” he was saying, asking people whether they would be ready to formally commit, those sources said.

Greg Kelly did not respond to a request for comment. Morgenthau, Trippi, Rollins, McCarthy, Wolfson, Schoen and Tusk declined comment. Goeas confirmed he spoke with Rollins about the race.

The poll from longtime Bloomberg pollster Doug Schoen found Kelly had huge name-recognition and was popular, but had too steep a hill to climb. The Schoen poll didn’t show the depth of Bloomberg fatigue among New York voters. Nor did it show just how much momentum there would be against the stop-and-frisk policy Kelly oversaw — it had become an issue in the primary, but the court ruling striking it down was still a month away. That ruling has now stayed and a different judge assigned, but there’s no telling whether Kelly would have been better able to defend the policy or explain it as one among many if he’d been a candidate, or would have been overwhelmed by the issue.

Even among those who entertained a Kelly campaign, the sense now is that an election with him in it would likely have become a referendum on stop-and-frisk, and the turns of the campaign might have undercut the significance of what he’d accomplished as police commissioner.

“It’s partly the mechanics, but more, just this was not his time. And obviously, the polling right now shows that,” said one of the people who spoke with Kelly. “Ray will go out as the greatest police commissioner in New York City history, as opposed to a candidate who ran and lost.”